1-Iodohexane → 5-(Hexyloxy)-2-methyl-1H-indole-3-acetic acid

HRID 37707

Reaction equation

HRID 37707 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[CH2:12][C:13]([OH:15])=[O:14].C[O-].[Na+].[CH2:19](I)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CO>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[CH2:12][C:13]([OH:15])=[O:14])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 125271-IodohexaneHCID 10942334Sodium MethoxideHCID 11310252O-Desmethyl-N-deschlorobenzoyl Indomethacin

Product 1

HCID 199357575-(Hexyloxy)-2-methyl-1H-indole-3-acetic acidYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-hydroxy-2-methyl-1H-indole-3-acetic acid (7.17 g, 35.0 mmol) in methanol (40 mL) is added sodium methoxide (70 mmol). The solution is evaporated, dimethylformamide (40 mL) is added followed by hexyl iodide (35.0 mmol). After 2 days the solvent is removed and the residue is partitioned between ethyl acetate and pH=4 buffer. The organic layer is separated, dried over MgSO4 and evaporated to 8.6 g of a brown solid. Recrystallization from ethanol/water affords 6.23 g (62%) of white crystals, m.p. 65°-67° C.

Workup

  1. customThe solution is evaporated
  2. additiondimethylformamide (40 mL) is added
  3. customAfter 2 days the solvent is removed
  4. customthe residue is partitioned between ethyl acetate and pH=4 buffer
  5. customThe organic layer is separated
  6. dry with materialdried over MgSO4
  7. customevaporated to 8.6 g of a brown solid
  8. customRecrystallization from ethanol/water

Sources & evidence

ORD record
ord-2918c717de254b449985b0c368a94450
Source dataset
uspto-grants-1995_05
Patent number
US05420289

Linked notes

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